CH223HW3 - qualify as organometallic compounds. (a)...

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Unformatted text preview: qualify as organometallic compounds. (a) Cyclopentyllithium (b) Ethoxymagnesium chloride (c) 2-Phenylethylmagnesium iodide (d) Lithium divinylcuprate 14.16 (e) Sodium carbonate (f) Benzylpotassium (g) Lithium diisopropylamide Suggest appropriate methods for preparing each of the following compounds from the CH223-001/003 of Spring 2012 starting material your choice. (a) CH3CH2CH2CH2CH2MgI Due CMgI Feb. 9 (c) CH3CH2CH2CH2CH2Li (d) (CH3CH2CH2CH2CH2)2CuLi Homework 3CH2C (b) CH3 (003) or Feb. 10 (001) 14.17 Which compound All problems taken fin eachCarey, 8th edition, and used into have the more polar the Fair rom of the following pairs would you expect compliance with carbon–metal bond? Use exclusion ofi copyright)protection. Please do not reproduce or distribute. (a) CH CH L or (CH CH Al 3 2 3 23 (b) (CH3)2Zn or (CH3)2Mg (c) CH3CH2MgBr or HC CMgBr Write the structure of the principal organic product of each of the following reactions: (a) 1-Bromopropane with lithium in diethyl ether (b) 1-Bromopropane with magnesium in diethyl ether (c) 2-Iodopropane with lithium in diethyl ether (d) 2-Iodopropane with magnesium in diethyl ether (e) Product of part (a) with copper(I) iodide 11/10/09 9:20:02 AM elhi3 of part (e) with 1-bromobutane /Users/elhi3/Documents/Smart Connection/InDesign/41332 (f) Product 11/10/09 9:20:02 AM elhi3 /Users/elhi3/Documents/Smart Connection/InDesign/41332 (g) Product of part (e) with iodobenzene (h) Product of part (b) with D2O and DCl (i) Product of part (c) with D2O and DCl ( j) Product of part (a) with formaldehyde in diethyl ether, followed by dilute acid Chapter k) Product of part (b) with benzaldehyde in diethyl ether, followed by dilute acid ( 14 Organometallic Compounds Chapter 14 Organometallic Compounds 14.18 indd Page 640 indd Page 640 14.19 14.19 14.20 14.20 14.21 14.21 (l) Product of part (c) with cycloheptanone in diethyl ether, followed by dilute acid (l) Product of part (c) with cycloheptanone in diethyl ether, followed by dilute acid O O X X (m) Product of part (d) with CH3CCH2CH3 in diethyl ether, followed by dilute acid (m) Product of part (d) with CH3CCH2CH3 in diethyl ether, followed by dilute acid (n) 1-Octene with diiodomethane and zinc–copper couple in diethyl ether (n) 1-Octene with diiodomethane and zinc–copper couple in diethyl ether (o) (E)-2-Decene with diiodomethane and zinc–copper couple in diethyl ether (o) (E)-2-Decene with diiodomethane and zinc–copper couple in diethyl ether (p) (Z)-3-Decene with diiodomethane and zinc–copper couple in diethyl ether (p) (Z)-3-Decene with diiodomethane and zinc–copper couple in diethyl ether Using 1-bromobutane and any necessary organic or inorganic reagents, suggest ef cient Using 1-bromobutane and any necessary organic or inorganic reagents, suggest ef cient syntheses of each of the following alcohols: syntheses of each of the following alcohols: (a) 1-Pentanol (c) 1-Phenyl-1-pentanol (a) 1-Pentanol (c) 1-Phenyl-1-pentanol (b) 2-Hexanol (d) 1-Butylcyclobutanol (b) 2-Hexanol (d) 1-Butylcyclobutanol Using bromobenzene and any necessary organic or inorganic reagents, suggest ef cient Using bromobenzene and any necessary organic or inorganic reagents, suggest ef cient syntheses of each of the following: syntheses of each of the following: (a) Benzyl alcohol (d) 4-Phenyl-4-heptanol (a) Benzyl alcohol (d) 4-Phenyl-4-heptanol (b) 1-Phenyl-1-hexanol (e) 1-Phenylcyclooctanol (b) 1-Phenyl-1-hexanol (e) 1-Phenylcyclooctanol (c) Bromodiphenylmethane (f) trans-2-Phenylcyclooctanol (c) Bromodiphenylmethane (f) trans-2-Phenylcyclooctanol Analyze the following structures so as to determine all the practical combinations of Analyze reagent and carbonyl compound that will all rise to each: Grignard the following structures so as to determinegivethe practical combinations of Grignard reagent and carbonyl compound that will give rise to each: (a) CH3CH2CHCH2CH(CH3)2 (d) 6-Methyl-5-hepten-2-ol (a) CH3CH2CHCH2CH(CH3)2 (d) 6-Methyl-5-hepten-2-ol OH OH (b) (b) CH CH OH OH OCH3 OCH3 (e) (e) OH OH (c) (CH3)3CCH2OH (c) (CH3)3CCH2OH 14.22 A number of drugs are prepared by reactions in which carbon–carbon bond formation is A number of drugs are prepared by reactions be a reasonable last step in the synthesis of 14.22 the last step. Indicate what you believe wouldin which carbon–carbon bond formation is t ach of step. Indicate ehe last the following:what you believe would be a reasonable last step in the synthesis of each of the following: OH OH Meparfynol, a mild hypnotic or sleep-inducing agent (a) CH3CH2CC CH Meparfynol, a mild hypnotic or sleep-inducing agent (a) CH3CH2CC CH CH3 CH 14.22 A number of drugs are prepared by reactions in which carbon-carbon bond formation is the last step. Indicate what you believe would be a reasonable last step in the synthesis of the following: H3C OH HO CH3 H N H3C H3C OH meparfynol a mild hypnotic/ sleeping aid H3CO diphepanol an antitussive mestranol an estrogenic component of oral contraceptives H ...
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This note was uploaded on 03/03/2012 for the course CHEM 223 taught by Professor S during the Fall '10 term at N.C. State.

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